How to Tangle Roommates: The Beginning
by BlueWarrior 2.0
Summary: Modern Hiccup (Henry.) and Astird decide to move to Florida and meet their new roommates Modern Rapunzel (Rachel.) and Eugene. Lets see if these four become close friends.


**How to Tangle Roommates: The Beginning.**

 _Have had this idea for awhile and I just can't seem to get it out of my head._

 _What happens when a modern Hiccup (Henry.), Astrid, Rapunzel (Rachel.), and Eugene decide to live together? Looks like we're about to find out._

 _Enjoy, because I don't own squat._

 **Part I.**

Let's be honest, flying is really boring. So thats when a young Henry Haddock decided it was the right time to tell his lovely and beautiful girlfriend Astrid Hofferson a funny story from his childhood. Correction; Henry thought it was funny, Astrid…not so much.

"And that's the time Scott nearly cut my finger off with a machete, I'm actually surprised I've never told you this before." Henry told his currently jaw-dropped girlfriend.

Now Henry decided to tell this story right out of nowhere while Astrid was reading one of her many, many cheesy romance novels that Henry always made fun of, normally Astrid didn't want to be disturbed when she was reading but when her boyfriend's _funny_ story began with "Did I ever tell you about the time Scott nearly cut my finger off with a machete when we were ten?" The book practically dropped itself to the ground.

The story was exactly how it sounded. As a kid Henry lived near a wooded area in Berk, Chicago and he and Scott would venture in the forest as children. Henry's father decided to give them a machete to play around with which horrified Astrid but Henry said there was more. One day Scott decided to chop a branch in half and asked Henry to hold it; Henry, who practically worshipped his cousin at this time did so. Unfortunately during this time Scott had terrible aim and…lets just say that Henry still has the scar on his left index finger.

Astrid just sat there in silence, she needed to process the recent story she was recently told. After a solid minute she finally decided to speak.

"You actually listened to Snotlout after he told you to hold a brach while he was holding a razor sharp machete?" She asked her boyfriend. Scott came up with the name Snotlout in high school as a way to attract girls…..it didn't work well, at all.

"Well yeah." Henry nonchalantly replied until he noticed his girlfriend's shock.

"We we're ten Astrid, I was young, stupid and thought Scott was the coolest person so of course I did everything he told me to do" Henry defended. It was true, there was a time where Henry idolized his cousin Scott and tried to be like him. Overtime however Henry grew up and Scott did not and while they still maintained a friendly relationship Henry always had to make sure that his cousin was staying out of trouble.

"I'm just glad you grew up." Astrid said before picking her book back up and continued to read.

The couple sat in silence for a few seconds Henry was fake drumming with his hands and Astrid was deep into her book before Henry came to a realization.

"Now that you mention it, I never saw that machete again after that." It was true, that was Henry's last memory of the infamous machete.

This caused Astrid to pinch the arch of her nose.

"But why would your dad give you guys a machete to play with in the first place?" She asked.

"Well you know my dad Astrid, he did everything he could to turn me into the macho man that I never became. Still hasn't succeeded." Henry joked.

Astrid did NOT like this at all and shook her head.

"Stop it, you know how I feel about you putting yourself down all the time." She continued.

Henry let out a sigh and admitted defeat. He had a habit of being extremely self deprecating as a way of dealing with his issues, Astrid wasn't about to have this and made sure he never put himself down.

"Sorry force of habit, but you have to admit that i'm a lot better now then when we first started started dating." He assured Astrid as the latter gave him a small smile.

Astrid smiled back and gave him a light punch to his shoulder.

"I know, I just want YOU to know how much you rock and I wouldn't be doing this life changing event with anyone else." She said pointing to his chest to show that she means it.

Henry smiled at his girlfriend's confidence, she truly was his rock. The social to his anti social, the realistic to his dreamer, the who always believed in him and the one who was crazy enough to move to a completely different state with him.

Henry and Astrid were leaving their hometown of Berk, Chicago and were moving to the sunshine state of Florida.

The reason why?

"I'm so ready to get out of the cold weather." Astrid said with excitement.

"I gotta admit it'll be pretty nice to experience some actual good weather instead of the same old crappy endless winter that we're oh so used too." Henry said agreeing with the reason behind their move.

"You forgot devastating winter babe." Astrid laughed.

"Let me rephrase that, I never wanna see snow for as long as I live." Henry said in a serious tone.

This got the couple to laugh as they enjoyed the benefits of their move.

"Come here you." Henry told Astrid as the latter rested her head on his shoulder while the two watched the unique patters from the ground below.

They remembered how after Astrid got her degree from Northwestern University with a degree in Physical Therapy as well as graduating Summa Cum Laude. (Henry went to a neighboring trade school despite being offer acceptance to numerous colleges, he preferred working with his hands and couldn't bear to work in an office environment.) The two decided to move to Florida for a change in their life. A choice that shocked both their families but was still happily accepted by both parties.

It would however, still be awhile before they would move. So they decided to take a weekend to visit Florida because…

"You sure that we're making the right choice with meeting people from an ad?" Astrid asked in concern.

Henry smiled, his girlfriend always had to be the realistic one.

"Guess we won't know unless we meet them, I've been messaging one of them. She seems nice." Henry shrugged.

Astrid raised an eyebrow. She knew that Henry would never play around, but that still didn't stop her from wanting to mess with him.

"She?" She said in a fake worried tone.

"You been messaging the girl the whole time and never told me?, are you that tired of me Henry Haddock?" She asked in a slightly louder voice to cause people to notice.

It was at this moment that Henry started to freak out, he knew what Astrid was doing and grabbed her hand.

"Astrid you know she has boyfriend. Thats all she talks about, bit annoying actually. Thats why I made sure the ad read couples only." He said giving his other half an assured look.

Astrid giggled at Henry's panic. While she was just teasing him it was rather heartwarming to show how devoted he was to her.

"All right babe you've made your point, and you do REALLY mean the world to me." She said in satisfaction.

In response, Henry gave her a small kiss on the top of her forehead.

"And I've always appreciated that." He said before noticing the soft yawn that came out of Astrid's mouth.

"You know we still have an hour before we land, why don't you get some rest. You didn't sleep well last night." Henry told the blonde beauty while stroking her golden hair.

Astrid was about to say something but a yawn came out and she closed her eyes with a soft smile.

Henry smiled at the image. Astrid was the only one who truly understood him besides his beloved cat Toothless who was currently being watched by his adoptive Uncle Gobber.

So much so that when Astrid came home to their overprice run down studio apartment after an extremely rough day, Henry felt that it was the best time to ask her if she wanted to move to Orlando, something that he'd been dreaming about for awhile. After thinking about it for a few seconds she enthusiastically said yes, along with a hug then kissing which turned to….

A loud snore, that was sound that snapped Henry out of his inner thoughts. He loved the girl more than life itself but Henry was still amazed by Astrid's incredibly loud snoring.

"I still don't get how she instantly falls asleep like that." He said to himself. Henry was the kind of person who lay in bed and that's when his mind would go a mile a minute. It would take at least a half hour for him to finally go to sleep. Astrid however, did not have that problem.

He took advantage of his alone time by glancing at the messages with the girl he'd been talking to.

When they first decided to move, Henry found out real quick that Orlando was rather expensive and while he and Astrid made a decent living for their age. (Astrid was a licensed Personal Trainer and Hiccup was a trained mechanic.) They decided that it would be smarter to share a house with another couple. They posted an ad and after many weird and extremely uncomfortable responses, including one that almost made Astrid punch Henry's rather expensive laptop. They finally got a response from a seemly nice couple named Rachel and Eugene. He'd been back and forth with the Rachel and found out that they both had a lot in common as they both loved art and music. He hadn't really spoken to her boyfriend Eugene but from what Rachel has told him and it was a lot, he seemed like a chill person to be around.

Henry and Astrid were confident in this couple enough to spend the weekend with them to get to know the other couple and see if the living arrangement would work out. If not, then they would at least have a weekend in Florida to look back on.

After reminiscing for a bit, Henry decided to kill some time by whipping out his laptop and continue working on his passion project: A fantasy novel about dragons.

But before that, he decided to sent a message to one of his potential roommates.

"Looking forward to meeting you Rachel." Henry sent the message and continued working on his novel.

For as long as he could remember he was obsessed with Dragons and the Viking Age, something that Astrid was all too familiar with. To a point where about a year ago when they were watching a really crappy animated dragon movie that Hiccup disliked greatly, he said in anger "I could make a better story than that." To which Astrid responded in her usual to the point tone "So why don't you?"

Now a year later he finally had enough material to start on the actual project. While he enjoyed working as a mechanic as he preferred to work with his hands, Henry's true passion was writing and it was thanks to his blunt but supportive girlfriend that motivated him to finally fulfill his dream.

After about an hour typing, Henry felt satisfied with what he was working on before the flight attendant's voice announced that they would be landing in Orlando in a few minutes.

Henry took this opportunity to save his work, put his laptop away and face the difficult challenge of waking up his now drooling girlfriend.

"Wake up milady." Henry said in a soft voice.

Astrid didn't wake up, not even close to it.

"We're landing soon, time to get up." Henry said talking louder.

Astrid replied with a very loud snore.

By this time Henry was nudging his girlfriend to wake up but that women was still asleep.

Henry loud out a large sigh and knew what he had to do.

"She's gonna hate me for this, but its for her own good." He said with a hint of dread coming out in his voice.

He looked to find any nearby sensitive areas on Astrid's body and saw that her sides were open.

"God help me." Henry said before putting his hands in a claw formation and proceeded to dig his hands into Astrid's sides.

Astrid woke up with a squeal and started giggling uncontrollably.

Henry released Astrid's extremely ticklish body and dodged an unintentional slap, Astrid had no control in her movements when she was being tickled and it was a good thing he had become an expert at knowing where her body parts would move.

Once Astrid regain her composure she gave Henry a death glare, something that Henry knew too many times to count.

"Damn it Henry, you know how much I hate being woken up like that!" She said in a threatening tone.

"Well what other choice did I have Astrid?, you were passed out." Defended Henry who currently had his hands up in defeat.

Astrid opened her mouth to say something but retracted as he was right. Astrid was a heavy sleeper and waking her up could be a challenge, especially for Henry.

Instead of arguing, The Blonde Beauty let out a groan as she folded her arms. Few people knew about Astrid's secret and it was something she was not proud of.

"I really hate being ticklish." She fumed.

"Oh you're not that bad." Henry said while trying desperately to keep a straight face, this was obviously not true.

Astrid could tell through the lie and wasn't having any of Henry's sass.

"I freak out when people barely touch me, I can't get pedicures without kicking someone, Besides you seem to have a hard time keeping your hands to yourself dragon boy." Astrid pointed to Henry's chest as he merely shrugged it off,

He couldn't deny it; despite Astrid telling him countless times not to tickle her, he couldn't resist it, he enjoyed making Astrid laugh.

"Sometimes I just can't help myself." Henry said using his fingers to stroke Astrid's sensitive neck which caused her to freak.

She responded by smacking his hand, very hard.

"Wow, I totally one hundred percent saw that coming!" Henry cried in pain while holding his tender hand.

"Mmmhmm and what did we learn today Mr Henry Jay Haddock III?" Astrid asked in a stern tone.

Henry thought about it for a second and causally put an arm around her back.

"That the only reason I do what I do is because I love my girlfriend's laugh and want to hear it on a regular basis?" Henry replied with his infamous cheesy grin.

Astrid let out a sigh.

"You really drive me crazy sometimes Haddock, you know that right?." She asked while Henry was expecting more.

"And?" Henry asked leaning closer.

Astrid smiled and leaned closer as well.

"But I love you." She said as the two shared a quick kiss.

The plane landed which caused Astrid to tense up before Henry gave a comforting hand.

"Its okay, we've landed." Henry assured her.

"Sorry, I love flying but I really hate that part." Astrid said. She hated showing fear but it was an exception when she was around Henry.

"That just makes it more fun." Henry joked.

Once the flight attendant gave the okay to leave the plane everyone onboard was started to get off, including the young lovers.

"Showtime milady." Henry said getting up and grabbing his and Astrid's carry on.

"No turning back now." She said as they went down the plane aisle.

"Oh Henry did you get my book?" Astrid asked.

Henry smiled and looked at Astrid's novel that he was currently holding.

"You mean that cheesy romance novel that makes me wanna puke every time you tell me about it…Totally threw it out the window when you weren't looking."

This earned Henry a nice punch to the shoulder.

"What? They're stupid." He defended himself.

"Shut up and let's go see our future roommates." Astrid fumed as she took her book shoved it into her bag before exiting the plane and into the terminal.

Henry let out a small chuckle.

"She's so fun to piss off." He laughed.

And with that the young adult hoisted his bag over his shoulder and exited the plane.

"Here goes nothing." He simply stated before heading to the terminal to start his new phase in life.

Meanwhile.

In Orlando, young couple Rachel Corona and Eugene Fitzherbert were parking their car in Orlando International Airport parking garage. Rachel got out of car extremely happy and excited whereas Eugene wasn't; Not necessarily from meeting his future roommates, but more because they had to pay to park instead of just going to the pickup section.

"Raps I love you more than anything in the world, you're the reason I get out of bed in the morning. So I have to ask, Why the hell are we paying for parking when we can just pick them up once they land? Its free you know." Eugene asked as he locked his beloved car known to him as his "Flynn Rider."

Rachel giggled at her boyfriend's frustrations.

"Well I figured it would be better if we actually got know our potential roommates instead of just putting them in our car without knowing anything about them." Rachel replied practically skipping to the People Movers.

"Exactly; if we don't like them then we can just sayonara and call it a day, it's the perfect plan." Said a proud Eugene.

Rachel shook her head and smiled.

"Come on Eugene, our new friends are waiting for us." She said practically dragging a fuming Eugene by the arm.

 _What do you think guys? Will this living arrangement work out? Will the four like each other? Did Henry actually throw Astrid's crappy romance novel out the plane window?_

 **Find out more in Part II.**


End file.
